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15
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Boger D.L., Boyce C.W., Labrodi M.A., Sehon A.A., Jin Q. J. Am. Chem. Soc. 121:1999;54
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24
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0033579656
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Gupton J.T., Krumpe K.E., Burnham B.S., Webb T.M., Shuford J.S., Sikorski J.A. Tetrahedron. 55:1999;14515
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26
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0034697265
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28
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4344578701
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WO 0164635 A1, 2001.
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Boger, D. L. WO 0164635 A1, 2001.
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Boger, D.L.1
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33
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0347623391
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Álvarez, M.8
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35
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33751554339
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Bray B.L., Mathies P.H., Naef R., Solas D.R., Tidwell T.T., Artis D.R., Muchoswski J.M. J. Org. Chem. 55:1990;6317
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Bray, B.L.1
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Muchoswski, J.M.7
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36
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4344605899
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note
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2 and AcBr
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37
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4344691869
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The crude cleavage material was analysed by HPLC and HPLC-MS
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The crude cleavage material was analysed by HPLC and HPLC-MS
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-
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39
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4344650539
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Commercial 3-methoxyphenylboronic acid was used to find the best reaction conditions to be applied to the synthesis of lamellarins and derivatives
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Commercial 3-methoxyphenylboronic acid was used to find the best reaction conditions to be applied to the synthesis of lamellarins and derivatives
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-
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40
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4344564359
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note
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1H NMR spectrum of the crude mixture by the singlet at 7.29 ppm due to the pyrrole proton 5
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-
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41
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4344658108
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13C NMR of bisarylpyrroles 16b-16d were used to corroborate the introduction of the new aromatic ring
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42
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0034554740
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The 4-isoproxoxyphenylboronic acid
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The 4-isoproxoxyphenylboronic acid 15b was not commercial when we started this project. It was prepared from the p-iodophenol by protection with 2-iodopropane followed by boronic acid formation via halogen-metal interchange using nBuLi followed by reaction with trimethylboronate as described in Chaumeil H., Signorella S., Le Drian C. Tetrahedron. 56:2000;9655
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(2000)
Tetrahedron
, vol.56
, pp. 9655
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Chaumeil, H.1
Signorella, S.2
Le Drian, C.3
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43
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4344610978
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3 over the resin during 3 h allowed total recovery of the resin beads
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3 over the resin during 3 h allowed total recovery of the resin beads
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-
-
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44
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4344701047
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Cironi, P.; Cuevas, C.; Albericio, F.; Álvarez, M. Tetrahedron 2004, 60, 8669.
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(2004)
Tetrahedron
, vol.60
, pp. 8669
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Cironi, P.1
Cuevas, C.2
Albericio, F.3
Álvarez, M.4
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45
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4344710313
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3 as base and TBAF in THF or DMF, as described in solution in Ref. 6b, proved ineffective
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3 as base and TBAF in THF or DMF, as described in solution in Ref. 6b, proved ineffective
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-
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46
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4344648626
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note
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15 equiv. of NaH or 2 equiv. of LDA in dry THF at reflux for 24 h afforded, after cleavage, mixtures of 18a and 21a in which the alkylation product was obtained in 25% (NaH) and 30% (LDA) yield (HPLC-MS). Increasing the amount of LDA or the use of other bases did not improve the yield of 21a
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-
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47
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4344702592
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The compound was not isolated after trying different purification procedures on the crude cleavage material by semipreparative HPLC. The loss of material, probably by decomposition in the column
-
The compound was not isolated after trying different purification procedures on the crude cleavage material by semipreparative HPLC. The loss of material, probably by decomposition in the column
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-
-
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48
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4344678823
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3 and 18-crown-6 as base in DMF in a microwave at 100 °C and 30-40 W during 2 min
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3 and 18-crown-6 as base in DMF in a microwave at 100 °C and 30-40 W during 2 min
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-
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50
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0001743426
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Banwell M.G., Flynn B.L., Hockless D.C.R., Longmore R.W., Rae A.D. Aust. J. Chem. 52:1998;755
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(1998)
Aust. J. Chem.
, vol.52
, pp. 755
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Banwell, M.G.1
Flynn, B.L.2
Hockless, D.C.R.3
Longmore, R.W.4
Rae, A.D.5
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51
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4344594027
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3 and 18-crown-6 in DMF
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3 and 18-crown-6 in DMF
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-
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53
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0001140874
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1H NMR data were identical to those described in
-
1H NMR data were identical to those described in Menger F.M. Chem. Soc. Rev. 1:1972;229
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(1972)
Chem. Soc. Rev.
, vol.1
, pp. 229
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Menger, F.M.1
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